【摘要】：木脂素類化合物種類繁多,在自然界中分布廣泛,具有多種生物活性,是許多中藥的有效成分,但在植物中含量較低,提取困難,這些因素嚴(yán)重限制木脂素研究的進(jìn)展,故木脂素類化合物的合成研究受到了越來越多的關(guān)注,有關(guān)木脂素合成的報(bào)道也越來越多。本文主要對木脂素的定義,分類,分離純化,理化性質(zhì),合成研究現(xiàn)狀等方面進(jìn)行綜述,同時(shí),對兩種呋喃類木脂素化合物的全合成路線和最佳反應(yīng)條件進(jìn)行實(shí)驗(yàn)研究,主要內(nèi)容如下:第一部分,從木脂素的定義,命名,分離純化,分類,生物活性,理化性質(zhì),合成研究等方面對木脂素進(jìn)行系統(tǒng)的介紹,通過分析已報(bào)道的木脂素的合成路線和方法,提出了兩種呋喃類木脂素化合物的全合成路線和方法。第二部分,介紹了兩種呋喃類木脂素化合物的最佳合成路線,對2-甲基-(2E)-丁烯酸-(2S,3R,4R)-2-(3,4-二甲氧苯基)-4-(3,4-二甲氧芐基)-3-四氫呋喃甲酯進(jìn)行合成時(shí),是以廉價(jià)的藜蘆醛為原料,經(jīng)過Stobbe縮合反應(yīng),酯化反應(yīng),Aldol反應(yīng)等構(gòu)建木脂素骨架,再經(jīng)過兩步還原反應(yīng),酯化反應(yīng),最終得到目標(biāo)產(chǎn)物。對木脂素3-(4-羥基-3-甲氧基苯基)-(2E)-丙烯酸-(2S,3R,4R)-2-(4-羥基-3,5-二甲氧苯基)-4-[(4-羥基-3,5-二甲氧苯基)甲基]-3-四氫呋喃甲酯進(jìn)行合成時(shí),是以廉價(jià)的丁香醛為原料,依次經(jīng)過芐基保護(hù)反應(yīng),Stobbe縮合反應(yīng),酯化反應(yīng),羥醛縮合反應(yīng)構(gòu)建木脂素基本骨架,再經(jīng)過還原反應(yīng),脫水反應(yīng),酯化反應(yīng),脫保護(hù)反應(yīng)等最終得到目標(biāo)化合物。第三部分,對實(shí)驗(yàn)中的各步反應(yīng)進(jìn)行討論,通過篩選反應(yīng)中的催化劑,溶劑,反應(yīng)時(shí)間,反應(yīng)溫度,投料比等因素來確定最佳反應(yīng)條件,從而確定整個(gè)實(shí)驗(yàn)的最佳反應(yīng)路線。
[Abstract]:Lignans are widely distributed in nature and have a variety of biological activities. They are active components of many traditional Chinese medicines, but they are difficult to be extracted because of their low content in plants. These factors seriously limit the progress of lignin research. Therefore, more and more attention has been paid to the synthesis of lignans, and there are more and more reports on the synthesis of lignans. In this paper, the definition, classification, separation and purification, physicochemical properties and synthesis status of lignans were reviewed. At the same time, the synthesis routes and optimum reaction conditions of two kinds of furan lignans were studied experimentally. The main contents are as follows: in the first part, the definition, naming, separation and purification, classification, biological activity, physicochemical properties and synthesis of lignin are introduced systematically. Based on the analysis of the reported synthesis routes and methods of lignans, two total synthesis routes and methods of furan lignans were proposed. In the second part, the optimum synthetic routes of two furan lignans were introduced, and 2-methyl- (2e) -butenoic acid- (2Sf3R), 4R) -2- (3o 4- dimethoxyphenyl) -4- (3- 4- dimethoxybenzyl) -3- tetrahydrofuran methyl ester was synthesized from cheap resveratrol by Stobbe condensation and esterification. The lignin skeleton was constructed by Aldol reaction, then the target product was obtained by two step reduction reaction and esterification reaction. P-lignan 3- (4-hydroxy-3-methoxy phenyl)-(2e) -acrylic acid-(2Sn3R), p lignan 3- (4-hydroxy-3-methoxy phenyl)-(2e) -acrylic acid 4R) -2- (4- (4-hydroxy-3- (5-dimethoxyphenyl) -4- [(4-hydroxy-3-dimethoxyphenyl) methyl] -3-tetrahydrofuran methyl ester was synthesized from cheap eugenaldehyde, Through benzyl protection reaction, Stobbe condensation reaction, esterification reaction, hydroxaldehyde condensation reaction to form the basic skeleton of lignin, then through reduction reaction, dehydration reaction, esterification reaction, deprotection reaction and so on, the target compound was finally obtained. In the third part, the optimum reaction conditions are determined by screening the catalyst, solvent, reaction time, reaction temperature, feed ratio and so on, so as to determine the optimal reaction route of the whole experiment.
【學(xué)位授予單位】：青島科技大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：O636

【參考文獻(xiàn)】

相關(guān)期刊論文 前10條

1 孟瑾;杜利月;郭留城;;苯基萘類木脂素內(nèi)酯的化學(xué)合成[J];有機(jī)化學(xué);2016年11期

2 毛杰;于能江;楊郁;趙毅民;;二芐基丁內(nèi)酯類木脂素的生物活性研究進(jìn)展[J];國際藥學(xué)研究雜志;2014年03期

3 李桂秀;林夢感;楊國紅;楊義芳;秦雪梅;;草胡椒屬植物中木脂素類化合物及其生物活性研究進(jìn)展[J];中草藥;2012年09期

4 黃坤;蔣偉;趙紀(jì)峰;王昌華;劉翔;張植偉;秦松云;鐘國躍;;瀕危藥用植物桃兒七中鬼臼毒素和總木脂素含量測定[J];中國中藥雜志;2012年10期

5 黃坤;蔣偉;趙紀(jì)峰;劉翔;張植偉;王昌華;秦松云;鐘國躍;;桃兒七中木脂素類化學(xué)成分及其活性研究進(jìn)展[J];中藥新藥與臨床藥理;2012年02期

6 胡俊揚(yáng);陸兔林;毛春芹;蘇桃;蔡寶昌;;HPLC法同時(shí)測定不同產(chǎn)地五味子中8種木脂素類成分[J];中成藥;2012年02期

7 趙育;惠捷;朱俐;;天然糖苷Cleistanthin-B的合成[J];南通大學(xué)學(xué)報(bào)(自然科學(xué)版);2009年02期

8 張力子;姜英俊;焦曉臻;謝平;趙東保;;8,′8″-去甲基三白脂素-8的全合成[J];合成化學(xué);2008年06期

9 王豐玲;張英鋒;趙琳;鄭向軍;阮棟梁;馬子川;;木脂素的制備、用途和展望[J];渤海大學(xué)學(xué)報(bào)(自然科學(xué)版);2008年01期

10 汪秋安;張紅;王力;;新型苯并呋喃新木脂素類化合物的合成研究[J];湘潭大學(xué)自然科學(xué)學(xué)報(bào);2007年03期

相關(guān)碩士學(xué)位論文 前3條

1 李晨晨;Threo-(±)-3,4-二香草基四氫呋喃及其衍生物的合成研究[D];青島科技大學(xué);2016年

2 秦筱;聯(lián)苯環(huán)辛二烯木脂素類似物的設(shè)計(jì)和立體選擇性合成[D];北京工業(yè)大學(xué);2012年

3 于志紅;亞麻木脂素對小鼠免疫水平影響的研究[D];東北農(nóng)業(yè)大學(xué);2007年

，

本文編號：2357805